Do your elderly parents depend on the $1,000 you send them each month? Are your kids insured by your employer-based health care plan? If you’re spending money on others, ask yourself: Do I have siblings who could take turns sending money to Mom and Dad? Could the kids be listed on my spouse’s health plan? Which brings us to . . .
Find health insurance
If you’re leaving a job, it will likely be cheapest to be covered by your spouse’s plan. If that’s not an option, look into purchasing a policy individually or continuing your coverage through COBRA. To choose a personal policy, start at ehealthinsurance.com, the largest online health insurance market for individuals. If you are a small business shopping for yourself and employees, find a broker through the National Association of Health Underwriters at nahu.org.
That means exhausting your lowest interest rate options first: student loans and loans authorized by the Small Business Administration. Steer clear of home equity loans and lines of credit, because if your new venture doesn’t make it, your home will be on the line. Do not even think about robbing your retirement accounts: The potential penalties aren’t worth it.
Chart your exit strategy
Before you dive into Plan A, make sure you have a Plan B. Your success with a new vocation will depend on the economy as well as the health of the particular industry you choose, and neither is within your control. So if the seas get rough, can you easily return to your old profession or scale back your original game plan? Understand that not everything will go as expected—regardless of whether you have all your funding lined up, a supportive family and a no-brainer proposition. On the other hand, if you do have all that, you’re further ahead than most people. Good luck!
Jean Chatzky is More’s finance columnist and the author of several books. Read more of her advice here.